(S)-(-)-2-methoxymethyl-1-(2-methylthio-1-ethylidenamino)-pyrrolidine | 155996-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(-)-2-methoxymethyl-1-(2-methylthio-1-ethylidenamino)-pyrrolidine
• 英文别名: (E)-N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylsulfanylethanimine
• CAS: 155996-64-8
• 化学式: C₉H₁₈N₂OS
• 分子量: 202.321
• InChiKey: ZSEIMKHCVKIBSN-UMYFRRCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-methoxymethyl-1-(2-methylthio-1-ethylidenamino)-pyrrolidine 、 alkaline earth salt of/the/ methylsulfuric acid 在 lithium diisopropyl amide 作用下， 生成 (S,R)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine 、 (S,S)-(-)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones

  摘要：

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.

  DOI：

  10.1016/s0040-4020(01)87015-0
• 作为产物：
  描述：

  二甲基二硫 、 (S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine 在 lithium diisopropyl amide 作用下， 生成 (S)-(-)-2-methoxymethyl-1-(2-methylthio-1-ethylidenamino)-pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones

  摘要：

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.

  DOI：

  10.1016/s0040-4020(01)87015-0